4-Methylmorpholine → HCID 127261982, compound

HRID 1768873Notes

Reaction equation

HRID 1768873 reaction equation
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=O)[CH2:3][CH:4]([CH3:6])[CH3:5].[NH:17]([CH3:29])[C@H:18]([C:26]([NH2:28])=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CN1CCOCC1>O1CCCC1>[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([N:17]([CH3:29])[C@H:18]([C:26]([NH2:28])=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:9])[CH2:3][CH:4]([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 10702467Nalpha-Methyl-L-phenylalaninamide

Product 1

HCID 127261982HCID 127261982, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Condensation of Boc-Leu-OH (liberated from 5.0 g. of the monohydrate by heating at 45° C. under vacuum) and H-MePhe-NH2 and H-MepheNH2 (mixture of isomers) hydrobromide salt (4.92 g.) and N-methylmorpholine (two 2.31 g. portions) in tetrahydrofuran (50 ml.) for 45 min. at 25° C. and then overnight at room temperature, isolation of the crude product (5.94 g.) by ethyl acetate extraction, and purification by HPLC on silica gel gave Boc-Leu-MePhe-NH2 and Boc-Leu-Mephe-NH2 (mixture of isomers) as a colorless foam (3.8 g., 48% yield).

Workup

  1. extractionovernight at room temperature, isolation of the crude product (5.94 g.) by ethyl acetate extraction, and purification by HPLC on silica gel

Sources & evidence

ORD record
ord-b71ba64ac17a4ab29c7aada7da9201bf
Source dataset
uspto-grants-1995_01
Patent number
US05378803

Reaction notes

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